catena-Poly[[(1,10-phenanthroline)manganese(II)]-μ(3)-5-methyl-isophthalato].

In the title coupound, [Mn(C(9)H(6)O(4))(C(12)H(8)N(2))](n), the Mn(II) ion is coordinated by two N atoms [Mn-N = 2.273 (3) and 2.305 (2) Å] from a 1,10-phenanthroline ligand and four O atoms [Mn-O = 2.112 (2)-2.343 (3) Å] from three 5-methyl-isophthalate (mip) ligands in a distorted octa-hedral geometry. Each mip dianion acts as a tetra-dentate ligand connecting three Mn ions. The crystal packing exhibits π-π inter-actions [3.599 (2)-3.755 (2) Å] between the centroids of the six-membered rings of neighbouring 1,10-phenanthroline ligands.

Related literature

For crystal structure of related polymeric compound, see Nie et al. (2001 ▶). For details of the coordination abilities of 1,3-benzene­dicarboxyl­ate derivatives, see: Pan et al. (2006 ▶); Yang et al. (2002 ▶); Ma et al. (2008 ▶).

Experimental

Crystal data

[Mn(C9H6O4)(C12H8N2)]

M = 413.28

Monoclinic,

a = 9.2837 (11) Å

b = 10.3786 (13) Å

c = 18.824 (2) Å

β = 101.372 (2)°

V = 1778.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 295 (2) K

0.19 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.847, T max = 0.948

13275 measured reflections

3313 independent reflections

2230 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.097

S = 1.02

3313 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036362/cv2471sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036362/cv2471Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C9H6O4)(C12H8N2)]	F000 = 844
Mr = 413.28	Dx = 1.544 Mg m−3
Monoclinic, P2/c	Mo Kα radiation λ = 0.71073 Å
a = 9.2837 (11) Å	Cell parameters from 1788 reflections
b = 10.3786 (13) Å	θ = 2.3–19.8º
c = 18.824 (2) Å	µ = 0.77 mm−1
β = 101.372 (2)º	T = 295 (2) K
V = 1778.1 (4) Å3	Block, yellow
Z = 4	0.19 × 0.10 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	3313 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.056
T = 295(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.847, Tmax = 0.948	k = −12→12
13275 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0334P)2 + 0.7839P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3313 reflections	Δρmax = 0.26 e Å−3
254 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Mn1	0.36904 (5)	0.31882 (4)	0.32302 (2)	0.03865 (16)
O1	0.3711 (3)	0.4040 (3)	0.42907 (12)	0.0685 (8)
O2	0.1789 (3)	0.2896 (3)	0.38683 (13)	0.0757 (8)
O3	0.2707 (2)	0.5464 (2)	0.74411 (11)	0.0480 (6)
O4	0.4110 (3)	0.6197 (2)	0.67041 (11)	0.0548 (6)
N1	0.4764 (3)	0.1298 (3)	0.36551 (15)	0.0520 (7)
N2	0.2489 (3)	0.1543 (2)	0.25312 (13)	0.0443 (7)
C1	0.1932 (3)	0.3809 (3)	0.50355 (15)	0.0385 (7)
C2	0.2745 (3)	0.4529 (3)	0.55968 (15)	0.0362 (7)
H2	0.3655	0.4860	0.5554	0.043*
C3	0.2200 (3)	0.4753 (3)	0.62196 (15)	0.0353 (7)
C4	0.0818 (3)	0.4276 (3)	0.62701 (16)	0.0407 (8)
H4	0.0450	0.4437	0.6687	0.049*
C5	−0.0017 (3)	0.3569 (3)	0.57130 (17)	0.0441 (8)
C6	0.0567 (4)	0.3342 (3)	0.51018 (16)	0.0449 (8)
H6	0.0026	0.2861	0.4724	0.054*
C7	0.2510 (4)	0.3568 (3)	0.43524 (16)	0.0458 (8)
C8	0.3075 (4)	0.5517 (3)	0.68310 (16)	0.0387 (7)
C9	−0.1512 (4)	0.3073 (4)	0.5774 (2)	0.0629 (10)
H9A	−0.2236	0.3411	0.5383	0.094*
H9B	−0.1736	0.3344	0.6228	0.094*
H9C	−0.1516	0.2149	0.5751	0.094*
C10	0.5876 (4)	0.1195 (4)	0.4209 (2)	0.0795 (13)
H10	0.6301	0.1942	0.4430	0.095*
C11	0.6440 (5)	−0.0001 (5)	0.4477 (3)	0.1003 (17)
H11	0.7215	−0.0045	0.4873	0.120*
C12	0.5841 (5)	−0.1089 (5)	0.4151 (3)	0.0919 (15)
H12	0.6213	−0.1887	0.4323	0.110*
C13	0.4680 (4)	−0.1032 (4)	0.3564 (2)	0.0641 (11)
C14	0.3982 (5)	−0.2131 (4)	0.3178 (3)	0.0758 (13)
H14	0.4325	−0.2952	0.3318	0.091*
C15	0.2853 (5)	−0.1995 (4)	0.2624 (3)	0.0759 (13)
H15	0.2421	−0.2729	0.2390	0.091*
C16	0.2290 (4)	−0.0773 (3)	0.2381 (2)	0.0576 (10)
C17	0.1094 (5)	−0.0582 (5)	0.1816 (2)	0.0809 (13)
H17	0.0633	−0.1288	0.1565	0.097*
C18	0.0596 (5)	0.0622 (5)	0.1628 (2)	0.0765 (12)
H18	−0.0222	0.0746	0.1260	0.092*
C19	0.1331 (4)	0.1674 (4)	0.19962 (17)	0.0576 (10)
H19	0.0995	0.2499	0.1861	0.069*
C20	0.2954 (4)	0.0339 (3)	0.27317 (17)	0.0428 (8)
C21	0.4156 (4)	0.0209 (3)	0.33261 (18)	0.0475 (9)

	U11	U22	U33	U12	U13	U23
Mn1	0.0482 (3)	0.0372 (3)	0.0286 (2)	−0.0040 (2)	0.0030 (2)	−0.0008 (2)
O1	0.0677 (18)	0.093 (2)	0.0506 (15)	−0.0197 (16)	0.0247 (14)	−0.0229 (14)
O2	0.0743 (18)	0.103 (2)	0.0479 (15)	−0.0192 (16)	0.0075 (14)	−0.0337 (15)
O3	0.0631 (15)	0.0485 (14)	0.0331 (12)	−0.0072 (11)	0.0111 (11)	−0.0046 (10)
O4	0.0553 (15)	0.0618 (15)	0.0442 (13)	−0.0182 (13)	0.0023 (11)	−0.0025 (12)
N1	0.0442 (17)	0.0498 (18)	0.0580 (18)	−0.0018 (14)	0.0003 (15)	0.0111 (15)
N2	0.0490 (17)	0.0452 (18)	0.0376 (15)	−0.0063 (13)	0.0055 (13)	−0.0031 (12)
C1	0.0432 (19)	0.0382 (18)	0.0318 (16)	0.0036 (15)	0.0014 (14)	0.0011 (14)
C2	0.0366 (17)	0.0352 (17)	0.0353 (16)	0.0021 (14)	0.0034 (14)	0.0031 (13)
C3	0.0391 (18)	0.0339 (17)	0.0301 (16)	0.0010 (14)	0.0000 (14)	0.0009 (13)
C4	0.0441 (19)	0.0441 (19)	0.0336 (17)	0.0037 (15)	0.0070 (15)	0.0064 (14)
C5	0.0397 (19)	0.0421 (19)	0.046 (2)	−0.0038 (15)	−0.0016 (16)	0.0100 (15)
C6	0.051 (2)	0.0423 (19)	0.0366 (18)	−0.0012 (16)	−0.0038 (16)	−0.0023 (15)
C7	0.053 (2)	0.049 (2)	0.0314 (17)	0.0088 (17)	−0.0008 (16)	−0.0032 (15)
C8	0.044 (2)	0.0355 (18)	0.0336 (17)	0.0004 (15)	0.0019 (15)	0.0017 (14)
C9	0.045 (2)	0.074 (3)	0.066 (2)	−0.016 (2)	0.0016 (18)	0.012 (2)
C10	0.068 (3)	0.074 (3)	0.082 (3)	−0.001 (2)	−0.018 (2)	0.016 (2)
C11	0.077 (3)	0.094 (4)	0.113 (4)	0.017 (3)	−0.023 (3)	0.038 (3)
C12	0.083 (3)	0.069 (3)	0.121 (4)	0.025 (3)	0.014 (3)	0.040 (3)
C13	0.061 (3)	0.050 (2)	0.086 (3)	0.013 (2)	0.030 (2)	0.017 (2)
C14	0.091 (3)	0.031 (2)	0.119 (4)	0.009 (2)	0.054 (3)	0.007 (2)
C15	0.094 (3)	0.046 (3)	0.099 (3)	−0.011 (2)	0.045 (3)	−0.018 (2)
C16	0.070 (3)	0.042 (2)	0.069 (3)	−0.0120 (19)	0.032 (2)	−0.0112 (18)
C17	0.096 (4)	0.071 (3)	0.071 (3)	−0.025 (3)	0.006 (3)	−0.026 (2)
C18	0.076 (3)	0.086 (3)	0.060 (3)	−0.025 (3)	−0.004 (2)	−0.015 (2)
C19	0.064 (2)	0.061 (2)	0.043 (2)	−0.012 (2)	−0.0016 (19)	−0.0031 (17)
C20	0.047 (2)	0.040 (2)	0.0439 (19)	−0.0033 (16)	0.0165 (16)	−0.0064 (15)
C21	0.048 (2)	0.041 (2)	0.060 (2)	−0.0015 (16)	0.0276 (18)	0.0062 (17)

Mn1—O3i	2.112 (2)	C5—C6	1.385 (4)
Mn1—O4ii	2.120 (2)	C5—C9	1.505 (4)
Mn1—O1	2.180 (2)	C6—H6	0.9300
Mn1—N1	2.273 (3)	C9—H9A	0.9600
Mn1—N2	2.305 (2)	C9—H9B	0.9600
Mn1—O2	2.343 (3)	C9—H9C	0.9600
Mn1—C7	2.595 (3)	C10—C11	1.402 (5)
O1—C7	1.244 (4)	C10—H10	0.9300
O2—C7	1.235 (4)	C11—C12	1.352 (6)
O3—C8	1.262 (3)	C11—H11	0.9300
O3—Mn1iii	2.112 (2)	C12—C13	1.385 (6)
O4—C8	1.252 (3)	C12—H12	0.9300
O4—Mn1ii	2.120 (2)	C13—C21	1.418 (5)
N1—C10	1.319 (4)	C13—C14	1.435 (5)
N1—C21	1.357 (4)	C14—C15	1.332 (5)
N2—C19	1.327 (4)	C14—H14	0.9300
N2—C20	1.351 (4)	C15—C16	1.414 (5)
C1—C6	1.385 (4)	C15—H15	0.9300
C1—C2	1.390 (4)	C16—C17	1.392 (5)
C1—C7	1.509 (4)	C16—C20	1.410 (4)
C2—C3	1.385 (4)	C17—C18	1.355 (6)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.396 (4)	C18—C19	1.397 (5)
C3—C8	1.498 (4)	C18—H18	0.9300
C4—C5	1.386 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.423 (4)
Cg1···Cg2iv	3.709 (2)	Cg3···Cg3iv	3.599 (2)
Cg2···Cg2v	3.755 (2)
O3i—Mn1—O4ii	96.85 (9)	O2—C7—C1	119.3 (3)
O3i—Mn1—O1	107.46 (10)	O1—C7—C1	119.4 (3)
O4ii—Mn1—O1	89.43 (9)	O2—C7—Mn1	64.41 (18)
O3i—Mn1—N1	156.59 (10)	O1—C7—Mn1	56.88 (17)
O4ii—Mn1—N1	83.61 (9)	C1—C7—Mn1	175.9 (2)
O1—Mn1—N1	95.94 (11)	O4—C8—O3	123.6 (3)
O3i—Mn1—N2	89.75 (9)	O4—C8—C3	118.1 (3)
O4ii—Mn1—N2	127.49 (9)	O3—C8—C3	118.3 (3)
O1—Mn1—N2	137.66 (10)	C5—C9—H9A	109.5
N1—Mn1—N2	72.00 (10)	C5—C9—H9B	109.5
O3i—Mn1—O2	100.46 (9)	H9A—C9—H9B	109.5
O4ii—Mn1—O2	145.47 (8)	C5—C9—H9C	109.5
O1—Mn1—O2	56.93 (9)	H9A—C9—H9C	109.5
N1—Mn1—O2	91.74 (10)	H9B—C9—H9C	109.5
N2—Mn1—O2	82.42 (9)	N1—C10—C11	122.4 (4)
O3i—Mn1—C7	106.19 (9)	N1—C10—H10	118.8
O4ii—Mn1—C7	117.61 (10)	C11—C10—H10	118.8
O1—Mn1—C7	28.55 (9)	C12—C11—C10	119.1 (4)
N1—Mn1—C7	94.06 (10)	C12—C11—H11	120.5
N2—Mn1—C7	110.05 (10)	C10—C11—H11	120.5
O2—Mn1—C7	28.38 (9)	C11—C12—C13	120.8 (4)
C7—O1—Mn1	94.6 (2)	C11—C12—H12	119.6
C7—O2—Mn1	87.2 (2)	C13—C12—H12	119.6
C8—O3—Mn1iii	117.0 (2)	C12—C13—C21	117.1 (4)
C8—O4—Mn1ii	157.6 (2)	C12—C13—C14	124.9 (4)
C10—N1—C21	118.9 (3)	C21—C13—C14	118.0 (4)
C10—N1—Mn1	124.7 (3)	C15—C14—C13	121.3 (4)
C21—N1—Mn1	116.4 (2)	C15—C14—H14	119.4
C19—N2—C20	118.2 (3)	C13—C14—H14	119.4
C19—N2—Mn1	125.9 (2)	C14—C15—C16	122.1 (4)
C20—N2—Mn1	115.7 (2)	C14—C15—H15	119.0
C6—C1—C2	119.3 (3)	C16—C15—H15	119.0
C6—C1—C7	120.3 (3)	C17—C16—C20	116.8 (4)
C2—C1—C7	120.4 (3)	C17—C16—C15	124.3 (4)
C3—C2—C1	120.0 (3)	C20—C16—C15	118.9 (4)
C3—C2—H2	120.0	C18—C17—C16	120.7 (4)
C1—C2—H2	120.0	C18—C17—H17	119.6
C2—C3—C4	119.5 (3)	C16—C17—H17	119.6
C2—C3—C8	120.4 (3)	C17—C18—C19	118.8 (4)
C4—C3—C8	120.1 (3)	C17—C18—H18	120.6
C5—C4—C3	121.4 (3)	C19—C18—H18	120.6
C5—C4—H4	119.3	N2—C19—C18	122.7 (4)
C3—C4—H4	119.3	N2—C19—H19	118.6
C6—C5—C4	117.8 (3)	C18—C19—H19	118.6
C6—C5—C9	121.6 (3)	N2—C20—C16	122.7 (3)
C4—C5—C9	120.6 (3)	N2—C20—C21	117.8 (3)
C5—C6—C1	122.0 (3)	C16—C20—C21	119.5 (3)
C5—C6—H6	119.0	N1—C21—C13	121.8 (3)
C1—C6—H6	119.0	N1—C21—C20	118.1 (3)
O2—C7—O1	121.3 (3)	C13—C21—C20	120.1 (3)
O3i—Mn1—O1—C7	91.9 (2)	O4ii—Mn1—C7—O2	−171.05 (19)
O4ii—Mn1—O1—C7	−171.1 (2)	O1—Mn1—C7—O2	178.9 (3)
N1—Mn1—O1—C7	−87.6 (2)	N1—Mn1—C7—O2	−86.1 (2)
N2—Mn1—O1—C7	−17.9 (3)	N2—Mn1—C7—O2	−13.8 (2)
O2—Mn1—O1—C7	0.6 (2)	O3i—Mn1—C7—O1	−96.9 (2)
O3i—Mn1—O2—C7	−104.8 (2)	O4ii—Mn1—C7—O1	10.1 (2)
O4ii—Mn1—O2—C7	14.1 (3)	N1—Mn1—C7—O1	95.0 (2)
O1—Mn1—O2—C7	−0.6 (2)	N2—Mn1—C7—O1	167.3 (2)
N1—Mn1—O2—C7	95.3 (2)	O2—Mn1—C7—O1	−178.9 (3)
N2—Mn1—O2—C7	166.9 (2)	Mn1ii—O4—C8—O3	67.5 (7)
O3i—Mn1—N1—C10	139.9 (3)	Mn1ii—O4—C8—C3	−114.3 (5)
O4ii—Mn1—N1—C10	47.4 (3)	Mn1iii—O3—C8—O4	9.6 (4)
O1—Mn1—N1—C10	−41.4 (3)	Mn1iii—O3—C8—C3	−168.61 (19)
N2—Mn1—N1—C10	−179.7 (3)	C2—C3—C8—O4	17.0 (4)
O2—Mn1—N1—C10	−98.3 (3)	C4—C3—C8—O4	−162.1 (3)
C7—Mn1—N1—C10	−70.0 (3)	C2—C3—C8—O3	−164.7 (3)
O3i—Mn1—N1—C21	−43.1 (4)	C4—C3—C8—O3	16.1 (4)
O4ii—Mn1—N1—C21	−135.6 (2)	C21—N1—C10—C11	−0.9 (6)
O1—Mn1—N1—C21	135.7 (2)	Mn1—N1—C10—C11	176.0 (3)
N2—Mn1—N1—C21	−2.7 (2)	N1—C10—C11—C12	1.0 (8)
O2—Mn1—N1—C21	78.8 (2)	C10—C11—C12—C13	−0.4 (8)
C7—Mn1—N1—C21	107.1 (2)	C11—C12—C13—C21	−0.2 (7)
O3i—Mn1—N2—C19	−17.7 (3)	C11—C12—C13—C14	179.4 (4)
O4ii—Mn1—N2—C19	−116.2 (3)	C12—C13—C14—C15	178.9 (4)
O1—Mn1—N2—C19	98.4 (3)	C21—C13—C14—C15	−1.6 (6)
N1—Mn1—N2—C19	177.2 (3)	C13—C14—C15—C16	0.6 (6)
O2—Mn1—N2—C19	82.8 (3)	C14—C15—C16—C17	−178.6 (4)
C7—Mn1—N2—C19	89.4 (3)	C14—C15—C16—C20	0.6 (6)
O3i—Mn1—N2—C20	167.8 (2)	C20—C16—C17—C18	−1.0 (6)
O4ii—Mn1—N2—C20	69.3 (2)	C15—C16—C17—C18	178.2 (4)
O1—Mn1—N2—C20	−76.1 (3)	C16—C17—C18—C19	2.0 (7)
N1—Mn1—N2—C20	2.7 (2)	C20—N2—C19—C18	−1.1 (5)
O2—Mn1—N2—C20	−91.7 (2)	Mn1—N2—C19—C18	−175.5 (3)
C7—Mn1—N2—C20	−85.1 (2)	C17—C18—C19—N2	−0.9 (6)
C6—C1—C2—C3	1.2 (4)	C19—N2—C20—C16	2.1 (5)
C7—C1—C2—C3	179.5 (3)	Mn1—N2—C20—C16	177.1 (2)
C1—C2—C3—C4	−1.5 (4)	C19—N2—C20—C21	−177.3 (3)
C1—C2—C3—C8	179.4 (3)	Mn1—N2—C20—C21	−2.4 (4)
C2—C3—C4—C5	0.8 (4)	C17—C16—C20—N2	−1.1 (5)
C8—C3—C4—C5	179.9 (3)	C15—C16—C20—N2	179.6 (3)
C3—C4—C5—C6	0.3 (4)	C17—C16—C20—C21	178.4 (3)
C3—C4—C5—C9	−179.4 (3)	C15—C16—C20—C21	−0.9 (5)
C4—C5—C6—C1	−0.6 (5)	C10—N1—C21—C13	0.3 (5)
C9—C5—C6—C1	179.1 (3)	Mn1—N1—C21—C13	−176.9 (2)
C2—C1—C6—C5	−0.1 (5)	C10—N1—C21—C20	179.7 (3)
C7—C1—C6—C5	−178.4 (3)	Mn1—N1—C21—C20	2.5 (4)
Mn1—O2—C7—O1	1.1 (3)	C12—C13—C21—N1	0.3 (5)
Mn1—O2—C7—C1	−178.2 (3)	C14—C13—C21—N1	−179.3 (3)
Mn1—O1—C7—O2	−1.2 (4)	C12—C13—C21—C20	−179.2 (3)
Mn1—O1—C7—C1	178.1 (2)	C14—C13—C21—C20	1.3 (5)
C6—C1—C7—O2	−3.6 (5)	N2—C20—C21—N1	0.0 (4)
C2—C1—C7—O2	178.0 (3)	C16—C20—C21—N1	−179.5 (3)
C6—C1—C7—O1	177.0 (3)	N2—C20—C21—C13	179.4 (3)
C2—C1—C7—O1	−1.3 (5)	C16—C20—C21—C13	−0.1 (5)
O3i—Mn1—C7—O2	82.0 (2)